


Career Boy

by Rhonda



Series: The Career Boy Cinematic Universe [1]
Category: Kuroshitsuji | Black Butler
Genre: Alternate Universe - American, Alternate Universe - Modern Setting, Anal Sex, Best Friends, Clothed Sex, Deepthroating, Desk Sex, Enthusiastic Consent, F/M, Female Pronouns for Grell Sutcliff, Fluff and Smut, Friends With Benefits, Happy Sex, Minor Cuckquean, Office Sex, Oral Fixation, Oral Sex, Porn with Feelings, Semi-Public Sex, Smut, Trans Character, Trans Female Character, Under-Desk Blow Jobs
Language: English
Status: Completed
Published: 2020-06-30
Updated: 2020-06-30
Packaged: 2021-03-04 03:00:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,572
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24996499
Author URL: https://archiveofourown.org/users/Rhonda/pseuds/Rhonda
Summary: Grelle Sutcliff fucks up on the job a lot and isn't exactly a model employee, luckily her best friend and boss William T. Spears is always looking out for her.She plans a special night of love making as a way to thank him after he sticks his neck out on her behalf for the bajillionth time.
Relationships: William T. Spears/Grell Sutcliff
Series: The Career Boy Cinematic Universe [1]
Series URL: https://archiveofourown.org/series/1824865
Comments: 2
Kudos: 16





	Career Boy

It was Grelle’s third day of her Double Secret Probation after she had massively fucked up the Whitechapel Tech merger. It was an accident that she’d spilled coffee down the front of their CEO’s red skirt suit but she had looked at her like she’d been stabbed in the chest. Grelle had already been in hot water for her cavalier work ethic, if it wasn’t for her dear sweet William advocating on her behalf she’d probably already be applying for unemployment checks. He strode into their Branch Director’s office, spent nearly an hour with the door shut, and walked out to inform Grelle she was still employed, to which she hugged him and promised him lots of _special_ rewards for always stepping up to bat for her. It just so happened she had planned tonight to be the first of many. It really was an ask to always have her back since she was perpetually fucking up, and he otherwise had no patience for nonsense. 

It was eight in the evening and everyone else had left for home. The entire office was empty save for her, the cleaning staff, and the light that drifted through the foggy glass on the door to Will’s office. A pile of paperwork two feet high sat finished on her desk. She was terrible at filing records and had made truly abysmal time. Any other day she might have simply left or burned the paperwork and said that she lost it, but she had promised William she’d be good, at least until the heat died down. He on the other hand always stayed late, much to her chagrin, never wanting to come out for drinks with the rest of the office.

She leaned back in her ergonomic chair and stretched, looking out over the bay across to the city lights of Oakland, watching the floodlit shipping cranes offload some of the chattel arriving from overseas. One of the perks of boinking the boss was that her cubicle got to be right next to the window, really it was one of the only perks other than the boinking itself. Will was her fuckbuddy, best friend, and immediate supervisor. He didn’t have the power to fire her or promote her, but even if he did he was far too professional to ever let his sex life influence his buisness decsions. Honestly that cold efficient exterior only made her pine for his touch more.

She reached into her purse and pulled out a small rubber bulb with a tiny stiff nozzle along with a bottle of lube and headed to the bathroom to freshen her makeup and to make sure she was clean and ready. She had to make a quick detour to the breakroom to get some salt packets so she didn’t overhydrate her insides. They almost never did stuff in the office. The day he stuck his neck out for her she was ready to kiss the hell out of his face right then and there, only to be met with the palm of his hand squarely in her face. She knew he wanted to but was scared of public displays of affection. It wasn’t that he was ashamed of their relationship he said one night after she’d asked while they cuddled postcoitally. He had simply always been concerned about just how professional he was perceived. He wanted to be taken seriously and if people saw the way he’d act around her would it undermine that persona quite a bit. She understood what it was like to want to be seen a certain way, and didn’t blame him, although it didn’t stop her from trying to varying degrees of failure.

After she made sure she was thoroughly clean inside she stood up, covered two of her fingers with the lube, bent over, and pressed the chilly goop up to her entrance. She didn’t want to make him feel obligated to prep her during _his_ reward, even though she knew he would never mind using his mouth on her g-bussy (girl boypussy) but this was about him and how she could make him feel good. She closed her eyes at the sensation as the pads of her fingers slipped inside. Her kitty stirred eager to make contact with some man meat, but there wasn’t much short of his touch that could get her good and truly hard since her orchie. Grelle let out an involuntary squeak as the fingers bottomed out inside her, luckily there wasn’t anyone else in the bathroom to hear. She needed to not get too distracted with taking care of herself while she had such a man waiting for her only a few doors away.

She hadn’t worn panties all day to see if Will would notice. She didn’t know whether he did or not, his expression infinitely unreadable. Thankfully she hadn’t really needed to tuck in years with how effective hrt had been at softening her girly parts. She still did, of course, but even in the pencil skirt without her panties she was virtually unclockable all day. Not that she was ashamed about her status as a trans woman, but she still felt the pressure to pass to avoid the micro and macroaggressions she’d experienced early in her transition. She didn't like the idea of testing people's potential bigotry when it could be easily avoided.

“Knock Knock Will. I’m respecting your privacy by knocking but asserting my authority as your bff-sie by coming in anyway~!” she sang as she opened the door to his office. He was sitting there like he always was, eyes fixed to his work computer, cocobolo desk covered in neat little piles of papers. Behind him was a large glass window that looked out over the bay, similar to the view she had from her cubicle but somehow much grander just for being in his office. The whole room was packed with bookshelves full of important business bullshit interspersed with small tasteful modernist sculptures by local artists and was rather dim, lit only by a minimalist LED desk lamp that was worth something like six hundred dollars.

“Oh wow you’re still here huh, that’s a first,” he said, not looking up from his work. 

“I can’t believe you’d forget about the little surprise I said I’d have for you,” Grelle said indignantly as she sauntered over to lean on the side of his desk. 

“I didn’t forget, I could never forget you Grelle no matter how much I desperately try to,” William replied as he stood up and faced her. “Honestly, maybe I should fuck you here every night if that’s what manages to keep you from leaving early and have you actually finish your work.” Grelle liked that idea on principle, but the thought of having to stay till dark every night was more than she could bear even if it did come with the implicit dicking. Besides, their trysts were more special for the fact they didn’t happen every day.

“Oh you wound me, William, you’re so cruel. But of course you know that’s exactly what I can’t resist about you.” It was all in good fun, part of the rapport they had developed over their years of friendship and benefits since they had met in college. Both of them knew he didn’t mean it, and Grelle only had to look into his eyes to see how deeply he cared for her. He ran his hands from the base of her thigh up to gently grip at her ass through her pencil skirt.

“I thought you weren't wearing anything under here. When you so obviously dropped your files in front of me in the hallway earlier just so that you could bend over to pick them up I didn’t see any pantylines. But with your talents for concealing lumps beneath your skirt I couldn’t be quite so sure.”

“You really think I’m so obvious?” Grelle huffed, tugging on his black tie, walking her fingers up his chest to cup at his face and loosen his collar.

“I’m sure there’s no way the whole office doesn’t know you want to fuck me, my only hope is that they haven’t figured out that we do.” While his right hand dipped back down her to her thigh to slip back up underneath her skirt his left trailed up and down her back before sliding around to grab onto one of her small breasts. She didn’t mind their size and in fact thought she looked cuter with them like this, a sentiment that William wholeheartedly agreed with. He hungrily unbuttoned her blouse and lay little kisses around the crook of her neck. She threw her head back and gave a deep throaty moan at the way his hands moved over her body. He was practically all over her. Eventually he managed to get the blouse open and pulled it down and off of her shoulders. They were fairly broad for a woman but they elegantly sloped down to her delicate arms in a way that she knew drove William wild. 

William paused for a moment to take her in, eyes lingering on the way her hardening nipples looked through the thin white cottony cupless bra she wore which made her feel uncharacteristically bashful. He lowered his head to her chest and delicately took one of her nipples into his mouth through the thin fabric. He knew how sensitive she was and she squirmed and he softly rolled it between his teeth, pressing his lips up to the surrounding breast in little kisses. She threw her head to the side, as she knew the bulge in her pencil skirt would have become unmistakable. He pulled his head away at which she sighed both with relief from the overstimulation and an undeniable longing for it to return. 

He reached out and took her chin in his hand, and gently turned her back to face him. She looked up at him, eyes full of lust as he moved his hand across her face. She was embarrassed about it, but she really loved that he was taller than her, so many of the other men she’d had were the same height or shorter than her, only to get even smaller when she wore the heels that she loved. With Will she could wear her heels and still look up into his eyes. He played with her glasses chain for a moment before dropping his hand back down to her chin and pressing at her lips with the pad of his thumb. He probed into her mouth, running along the tips of her unnaturally sharp teeth and stopping to depress her tongue. She opened her mouth wide for him with a big “ah,” and he took her tongue between his thumb and forefinger. He softly tugged at it pulling it out of her mouth and slowly rubbing clockwise circles over her pallet as she moaned quietly. She really wanted him inside her, it didn’t matter what part or where, just that she could have some of him in her, to take her sweet William and keep some of him safe and warm inside her body.

She took three of his fingers into her mouth while looking up at him with big doey eyes. Her tongue ran across the underside of them pausing to play with the golden wedding ring. William’s wife knew about them. William had made it very clear to her the nature of the relationship he had to his best friend when they had started dating. Grelle was admittedly reluctant to share him with another woman at first, but she just loved Will so much and she couldn’t ignore just how happy being married and having children made him. Besides, she couldn’t have bore his children if she wanted to, which she desperately did. She shook her head gently to clear out the negative thoughts. She made a much better best friend with benefits than a wife. Besides she got to be the cool auntie Grelle who always brought them candy and let them play violent video games. She’d definitely buy them beer once they were teenagers.

Also tonguing his wedding ring, thinking about how much more passionate he was with her than his wife got her kitty hard as diamonds. She softly hooked her teeth around it and tugged feeling it catch on his knuckle and sucked hard at the fingers in her mouth. It was twenty four karats and as such barely tasted metallic at all. She tried to slip the tip of her tongue underneath it, feeling the vows etched into the inside. Yeah, not being married to the man was far superior since it meant she could cuckquean his wife like this. It gave her a vague sense of superiority to the cis woman that helped counteract some of her insecurities.

Grelle popped Will’s fingers out of her mouth and slowly pushed him back into his chair. She slid down his body until she was on her knees beneath his desk. He ran his hands through her soft long red hair, stopping to rub the tips of her ears between his thumb and forefinger like he did her tongue earlier. She really couldn’t wait any longer so she reached up to unzip his tightening slacks and fished her hand into his boxer briefs to pull out the boycock she’d been fixating on all day. It was already mostly stiff, with little trimmed tufts of black pubes poking out along with it. She’d love him and lust after his meat regardless of his size, but the fact that he was big definitely didn’t hurt. It made a stark contrast with her soft relatively below average kitty that she kept clean shaven. Then again, she was a girl, they were supposed to have different parts. He was uncircumcised like she was and he was girthy enough that her hand could barely fit around it. She realized she was drooling just holding the thing, and didn’t want to start losing her lipstick before she managed to get some on her best friend’s cock.

She opened her mouth and popped the head inside. He groaned and leaned back in his chair, clearly having been waiting for this all day like she had. She nimbly snaked her tongue underneath his foreskin and circled his tip before using her lips to peel it back as she dipped her head a little lower. As the tip bumped up against the entrance to her throat she stopped, not even half way down his shaft. She pressed her lips down trying to mark the spot on his cock with her red lipstick, tilting her head back and forth. After she was satisfied she sucked hard and bobbed back up and down to that point a few times. William let out an expletive along with her name and tightened his grip on her hair. He pushed her down, gently but firmly letting Grelle know that he was more than eager to take advantage of her talents.

She obliged him and smoothly let the tip of his cock slip into her throat, sliding all the way down until her face was flush with the cozy neat black bush poking out from his pants. She nuzzled into him savoring the feeling of having him all the way inside her. She made sure to mark this spot red with her lipstick before slowly pulling back to take a breath. As she did she was taken in by his smell. There was his fragrant cologne of course, one that she had given him as a birthday gift years ago that he let become his trademark scent, but this close to his center at this late in the day it was mixed wonderfully with a musky human odor that Grelle had to stop and breath in. At the absence of her movement he let out a small uncharacteristic whine and used his hands to encourage her back down him again, which she happily obliged. 

They continued like that for a while, Grelle taking him all the way inside her and then eventually coming back up for air before he would nudge her back down again. Meanwhile she let her hands explore his thighs. He had pulled down his pants a little further for comfort and it let her run her fingers through his black leg hair. He didn’t shave, but he did periodically come at them with an electric razor so they were all a uniform quarter of an inch long. She liked him hairy, but spending so much time with Grelle had long infected him with the personal grooming bug too. As she nuzzled once again into his bush she let her hand wander down towards his balls, cupping them delicately. There was a small part of her that missed having a pair of her own, but being with William so much sated that itch. She gave them a little squeeze and felt him twitch in her mouth and throat accompanied by a groan and another whisper of her name. She placed a couple fingers against his perineum and stroked it like she knew he loved. This place here was somewhere she knew he’d never share with his wife, it was all Grelle’s and she made sure he knew it.

She felt him clench gently at the touch and whine that he was cumming. She just hummed her loving approval and looked up at him as he held her head down at his base. 

At that exact moment their Branch Director respected William’s privacy by knocking but asserted his authority as his boss by coming in anyway. To his credit William didn’t startle nearly as much as Grelle would have were their roles reversed. Instead he smoothly addressed the man scooting his chair up to the desk so he couldn’t see that he had his pants around his thighs and his cock down his subordinate’s throat. Grelle would have gagged at the movement if she still could. Instead she tenderly and quietly let him slide out of her, quickly swallowing the cum that dribbled out, all the rest having gone straight down her throat. She just sat there silent as they talked, the last thing she wanted to do was ruin his reward sex by getting him in trouble. She honestly admired how easily he was able to shift back into work mode after having just tenderly throat fucked a pretty girl, perhaps he never left work mode. Seriously though, what the fuck was this other guy even doing here this late at night? She bet he was fucking someone too, she really couldn’t comprehend why anyone would want to actually stay at work strictly longer than they had to unless any hanky panky was involved.

It was probably only like five minutes but it really felt like Grelle had been under that desk forever, she felt like a jackass for leaving her phone in her purse back at her desk, she wanted to play some fucking Flappy Bird or something to kill the time but instead she had to listen to two boring as hell career men talk about TPS Reports or whatever, she didn’t really understand.

Eventually the two exchanged pleasantries and the intruder said he was heading home for the night. William waited until he couldn’t hear his footsteps anymore before he rolled his chair back and poked his head under the desk.

“You okay down there?” In the darkness of the room she couldn’t read his face, but his voice was filled with a moderate concern.

“Yeah, I’m just a little disappointed you don’t have any secret compartments down here or anything,” Grell said climbing out from under the desk, stretching and trying to work out the stiffness in her neck. “Should we pick up where we left off or was he too much of a boner-killer for you?”

“You know that work could never kill the mood for me, besides just seeing you in that bra is enough to get me ready for round two.” Grelle blushed, Will was never this nice to her in front of other people, but when they were alone he always had complements that got to her. He really loved her body, and she loved him for it. She embraced him and gave him a quick peck on the lips, and then another, and then another. Maybe just a little bit of tongue? Okay, a lot of tongue. Will pulled away smiling from the shower of kisses. “If you’re ready, I was thinking it might be nice to get a little rough and I just wanted to check with you first,” he inquired almost sheepishly.

“It’s your special reward sex, but of course I love it when you get rough with me my sweet darling Will,” Grelle said, pulling his stiffening cock back out of his undies, still marked with two red circles. She gave it a few pumps while she looked into his eyes with a grin she could barely contain, and he just smiled back at her putting his hands back on her ass where they belonged. His smile quickly turned into a smirk before he spun her around and bent her over the desk eliciting a loud “Oooohhh hohoho~!” from his partner.

Grelle’s face was pressed into a stack of papers she knew Will would later regret rumpling when she felt him flip up her pencil skirt. She squeaked when she felt his warm hand touch her heretofore neglected kitty. She had gone soft from the time spent in cocobolo purgatory but now his warm hand was coaxing her to stiffen eagerly. He ran his finger down her kitty, over her sensitive squishy bits, slowing along her perineum and further up to her still slick entrance. He teased at it a bit, sliding in with his finger easily thanks to her foresight. She squirmed a little at the intrusion which only further encouraged William adding a second and then third finger. He lightly prodded her prostate enticing progressively higher pitched squeaks out of the woman.

Just as soon as Grelle had gotten used to the feeling of Will’s fingers he removed them. She didn’t know what he was doing, but it took a while. She had been sitting there face down ass up for almost a minute when she decided to turn her head around and find out just what Will was planning. The moment she looked over her shoulder his palm met the side of her face and squished her down into the desk. He was looming over her in a way that was both deeply erotic and a little intimating. He pressed his legs into hers and spread them out as wide as they’d go. She felt his fully erect cock slide up underneath her kitty. Even like this his still dwarfed hers, it was strangely affirming, but more importantly incredibly sexy. She squirmed with the desire to be filled and he lowered his body on top of hers pressing her firmly into the surface of the desk.

“Impatient are we?” he growled into her ears. She tried to lean her head back to make contact with him but his hand still held her stiffly in place. 

“Yes, Willy I am, please fuck me. You know I’m not above begging,” she pouted, using the nickname hoping to provoke him into action. She wiggled her butt up against him as emphasis. It didn’t seem to work and he just breathed down the back of her neck lustily. “Come on, Will, what do I need to promise you?”

“I want you to be at work, on time, every day for the next month,” he whispered into her ear. She giggled until she realized he was being serious. She thought about protesting, but it really seemed like he held all the cards.

“Sure,” she sighed.

The feeling of his cock sliding out from below her made her twitch with lust. They really should try having sex just like that sometime. But for now all she could think about was the way his tip was pressed against her entrance. Without much fanfare he pressed inside her, slowly sinking to the hilt. Even with Grelle’s experience it still took a little getting used to. She just focused on the feeling of having him inside her, and how special that was. Her man, her favorite person, and she was able to take him inside her, give him shelter within her body the same as any woman. Oh, but it felt divine, and when he started moving she lost her vision. The sensation of him sliding in and out of her was all the stimulation her little brain could manage to process.

The desk shook with the force of each of Will’s powerful thrusts, and Grelle’s unfocused eyes found purchase on the cup of colorful pens that rattled in time with their bodies. She tried her best to keep up, but as overstimulated as she was she felt like she wasn’t being much more than a warm body to Will. Maybe that was just what he needed. It didn’t help once he started gnawing on her ear. As he did he muttered sweet nothings that she couldn’t quite make out and they mixed beautifully with the soft squeals that she ejaculated every time his tip slid along her prostate. It was easy to lose herself in the bliss and her eyes kept returning to that cup of rattling pens to help ground herself in this moment.

She could come untouched, but it was hard and William wanted to make sure she was taken care of so he slipped his arm underneath her sweat slick body to pet at her kitty. He took it between his fingers and slid them up and down the length, eventually moving on to pressing the heel of his palm into the base of her kitty and moving it around in little clockwise circles.

Eventually all the pressure building inside her reached its breaking point and she screamed out Will’s name as she came hard, the way she only could when he was inside her. Her body shook and she clenched around him sending him over the edge with her. 

They collapsed into a happy heap on top of the resilient and welcoming cocobolo. Eventually they’d both recover from their bliss and spend a few minutes cleaning each other up, and then a few more joking with one another. All in all it was eleven thirty by the time they managed to tear away from each other long enough to pack up and head to the lobby together. William’s wife would be steamed, and the thought pleased Grelle to no end.

For the first time in forever William actually walked with Grelle to the parking garage. She left him with a kiss on the cheek and a firm slap on the butt that he was in far too good of a mood to make any of his usual reprimands over. Grelle thought the little reward she had for her friend went very well and she couldn’t wait for the next one she had planned.

And true to her word she came into work on time every day for the next month. Well, give or take a few minutes to pick up Starbucks. But he didn’t mind, she’d always bring him some too.

**Author's Note:**

> They're explicitly American because I find those Briddish accents to be a real boner-killer, and I have no ability to empathize with anyone who lives near the Atlantic Ocean.
> 
> [Also watch the music video for Dorian Electra's Career Boy.](https://www.youtube.com/watch?v=MDDukLyXY-M)

**Works inspired by this one:**

  * [Time](https://archiveofourown.org/works/25680574) by [Fish_Mommy](https://archiveofourown.org/users/Fish_Mommy/pseuds/Fish_Mommy)




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